It: Welcome to Derry Sets the Stage for Pennywise’s Pre-Derry Past

It: Welcome to Derry (Image via Apple TV)

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The first season of It: Welcome to Derry has finished its run on HBO, but the story is just beginning. The finale, which aired on December 14, 2025, closed one chapter while opening the door to a much deeper exploration of Stephen King’s horror universe. The series is not just a prequel to the popular It films; it is building a multi-season bridge to another iconic King classic, creating a shared universe that expands the mythology of both stories.

By introducing key characters and concepts, the show lays the groundwork for future seasons that will travel further back in time. These planned stories promise to connect Derry’s haunted history with the terrifying events of a completely different King nightmare.

The Hanlon Family Arrival and a Missing Boy

The series begins in 1962, introducing viewers to a new group of characters facing the evil lurking in Derry. The central family is the Hanlons: Major Leroy Hanlon, his wife Charlotte, and their son Will. They move to the town just as a young boy named Matty Clements vanishes under mysterious circumstances.

Their arrival seems to trigger a series of strange and frightening events. Will, struggling to adapt to his new home, befriends a group of local kids, including Lilly Bainbridge, Teddy Uris, and Phil Malkin. These children soon find themselves investigating the disappearance and other eerie occurrences, such as hearing children singing from the sewers. The series establishes that the fear and violence in Derry are cyclical, happening every 27 years, which is a central part of Pennywise’s nature.

A Key Character Linking Two King Worlds

One of the most significant introductions in Welcome to Derry is Dick Hallorann, played by Chris Chalk. In this series, Hallorann is a young airman stationed at the Derry Air Force Base. He possesses telepathic and clairvoyant abilities, which he calls “shining,” and is recruited by the military to help locate a mysterious “weapon”.

“You can look at it and say he changed, that this is the story of a selfish guy who becomes selfless, but I also think that there’s another reading of it, which is that he was that person the entire time and didn’t know it,” said showrunner Jason Fuchs about Hallorann’s journey.

His story in Derry serves as an origin for the kind, gifted man viewers later meet in The Shining. By the end of the season, his experiences in Derry change him, setting him on a path that eventually leads him to work as a chef in a hotel. Stephen King fans know this journey culminates at the Overlook Hotel in Colorado, where he uses his shine to help the Torrance family. This directly confirms the series also serves as a prequel to Stanley Kubrick’s 1980 film The Shining.

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Pennywise’s New Understanding of Time

The season finale, titled “Winter Fire,” featured a major revelation about the clown’s perception of reality. During a confrontation, Pennywise told the character Marge Truman that he experiences all of time—past, present, and future—simultaneously. For him, tomorrow and yesterday are the same.

This revelation has huge implications. It means the Pennywise of 1962 is aware of his eventual defeat at the hands of the Losers’ Club in 2016, as shown in It Chapter Two. This knowledge appears to shape his actions. In the finale, he specifically targeted Marge after revealing a chilling truth to her: she is destined to become the mother of Richie Tozier, a key member of the Losers’ Club.

“The seed of your stinking loins and his filthy friends bring me my death,” Pennywise said to Marge.

This raises a terrifying question for potential future seasons: if Pennywise can perceive all timelines, could he actively try to change the past? Could he go back to earlier cycles in Derry’s history to target the ancestors of his future enemies before they are even born? This concept, hinted at by the characters themselves, provides a narrative mechanism for the show to explore earlier time periods.

The Plan for Future Seasons and Derry’s Dark History

While HBO has not officially announced a second season, the creators have a clear multi-season plan. They envision the series moving backward in time to explore Pennywise’s previous awakening cycles in Derry.

  • Season 2 is planned to be set in 1935, 27 years before the first season. This storyline would delve into another tragic event from Derry’s past: the Bradley Gang Massacre. This bloody gang shootout, referenced in both King’s novel and the first It film, was briefly mentioned in Season 1 when an old car linked to the massacre was discovered.
  • Season 3 would go back even further to 1908. This era would focus on the Kitchener Ironworks explosion, a factory disaster that killed 102 people, many of them children. This tragedy was also referenced in the first season.

Show creator Andy Muschietti confirmed that a potential second season would feature younger versions of some characters from the first season, connecting the timelines across decades.

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